Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations

Cara Cesario; Lawrence P Tardibono Jr; Marvin J Miller

doi:10.1016/j.tetlet.2010.04.006

Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations

Tetrahedron Lett. 2010 Jun 9;51(23):3053-3056. doi: 10.1016/j.tetlet.2010.04.006.

Authors

Cara Cesario¹, Lawrence P Tardibono Jr, Marvin J Miller

Affiliation

¹ The University of Notre Dame, Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556.

Abstract

Carbocyclic aminonucleosides and epi-4'-carbocyclic puromycin were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. Pd(0)/InI-mediated allylations of a formyl species were used to install the 4'-hydroxymethyl group. A tethered aminohydroxylation strategy was employed to install the cis-2',3'-aminoalcohol moiety with complete regio- and diastereocontrol.

Abstract

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